EP0011911A1 - A method for protecting the liquid components of a chemiluminescent system and a chemiluminescent light-generating system thus protected - Google Patents

A method for protecting the liquid components of a chemiluminescent system and a chemiluminescent light-generating system thus protected Download PDF

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Publication number
EP0011911A1
EP0011911A1 EP79301723A EP79301723A EP0011911A1 EP 0011911 A1 EP0011911 A1 EP 0011911A1 EP 79301723 A EP79301723 A EP 79301723A EP 79301723 A EP79301723 A EP 79301723A EP 0011911 A1 EP0011911 A1 EP 0011911A1
Authority
EP
European Patent Office
Prior art keywords
chemiluminescent
components
hydroperoxide
laminate
light
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP79301723A
Other languages
German (de)
French (fr)
Inventor
Michael Mckay Rauhut
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
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Filing date
Publication date
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Publication of EP0011911A1 publication Critical patent/EP0011911A1/en
Withdrawn legal-status Critical Current

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B15/00—Layered products comprising a layer of metal
    • B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B15/00—Layered products comprising a layer of metal
    • B32B15/20—Layered products comprising a layer of metal comprising aluminium or copper
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/32—Layered products comprising a layer of synthetic resin comprising polyolefins
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
    • B32B7/04—Interconnection of layers
    • B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • C09K11/07—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials having chemically interreactive components, e.g. reactive chemiluminescent compositions
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F21—LIGHTING
    • F21K—NON-ELECTRIC LIGHT SOURCES USING LUMINESCENCE; LIGHT SOURCES USING ELECTROCHEMILUMINESCENCE; LIGHT SOURCES USING CHARGES OF COMBUSTIBLE MATERIAL; LIGHT SOURCES USING SEMICONDUCTOR DEVICES AS LIGHT-GENERATING ELEMENTS; LIGHT SOURCES NOT OTHERWISE PROVIDED FOR
    • F21K2/00—Non-electric light sources using luminescence; Light sources using electrochemiluminescence
    • F21K2/06—Non-electric light sources using luminescence; Light sources using electrochemiluminescence using chemiluminescence
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2323/00—Polyalkenes
    • B32B2323/10—Polypropylene

Definitions

  • This invention relates to chemiluminescent compositions and to a method and packaging material for improving the storage stability of chemiluminescent components.
  • Chemiluminescence is obtained when certain chemiluminescent compounds, for instance oxalic-type compounds, such as oxalic acid esters, are contacted in the presence of a fluorescer with a hydrogen peroxide compound.
  • chemiluminescent compounds for instance oxalic-type compounds, such as oxalic acid esters
  • a fluorescer with a hydrogen peroxide compound.
  • chemiluminescent light devices which utilize these chemiluminescent systems are described in U.S. Patents 3,511,612 and 3,576,987.
  • a typical chemiluminescent device comprises a lightstick, i.e. a transparent or translucent flexible plastic outer tube of polyethylene or the like and within the outer tube a frangible glass inner tube.
  • the inner tube is filled with one component of a two-component system (usually the hydroperoxide oomponent) and the outer plastic tube is filled with the other component (oxalate plus fluorescer).
  • the outer flexible tube is bent, thereby breaking the glass tube to mix the two components within the transparent outer tube. Reaction of the mixture produces chemiluminescence and the tube transmits the lights.
  • chemiluminescent system In order for a chemiluminescent system to be practical it must be capable of storage for reasonable storage periods at temperatures above normal room temperature, for example, up to about 40°C, and in humid atmosphere, without undue deterioration, which would cause loss of light generating capacity when the system is activated for use.
  • the chemiluminescent component for example, the oxalic acid ester
  • Polyethylene has been the packaging material of choice for containing the oxalate component because of its low cost, ease of fabrication, and translucence.
  • the polyethylene tube must be protected from moisture and light by enclosing it in an aluminum foil envelope during storage, since polyethylene is not impervious to moisture. Since the hydroperoxide component would be sensitive to storage in polyethylene, deteriorating rapidly on storage therein even at ordinary room temperature, it is preferred to contain the hydroperoxide component in the sealed inner glass vial which floats in the fluid contents of the polyethylene outer tube.
  • Aluminum foil is a satisfactory wrapper for containing the polyethylene tube in storage, provided the wrapper does not develop any leakage by ruptures, pin holes or the like. There is some difficulty in sealing an aluminum foil wrapper to make it totally impervious to moisture.
  • the present invention employs packaging material for containing one or several of the liquid components in a chemiluminescent device.
  • This material is a laminate of aluminum foil and polypropylene film, bonded together preferably by means of a low molecular weight polypropylene adhesive.
  • Diaryl and dialkyl oxalates substituted with strong electronegative groups, may be used as the chemiluminescent component, as described in U.S. Patent 3,597,362.
  • the greatest light output is expected with the oxalates derived from phenols or alcohols having a pKa value lower than 7.0. Examples include:
  • Suitable organic solvents for example, dibutyl phthalate
  • rate-regulating catalysts are described in U.S. Patent 3,576,987.
  • the laminate is an aluminum foil bonded to a cast polypropylene film.
  • the polypropylene film has a thickness of about 0.5 to 4 mils, and contains a food grade antioxidant additive.
  • the bonding adhesive for the laminate preferably is a low molecular weight polypropylene.
  • a suitable laminate is available from American Can Co. under the Trade name Maraflex 7F.
  • At least one of the chemiluminescent components is stored in a container made of the laminate with the contents in contact with the polypropylene surface of the laminate material.
  • the laminate is not suitable for use as a material for the outer container of a lighting device, because it cannot transmit chemiluminescence.
  • the laminate is nonetheless useful as a storage container for one or several of the liquid chemiluminescent components in a chemiluminescent device to protect the contents from light, air and moisture.
  • a package made of the laminate material can be used in lighting devices of diverse shapes and designs, provided that the construction of the lighting device comprises means to rupture the laminate package and allow the contents thereof to mix and react to produce chemiluminescence within a translucent outer container.. Devices of this kind were described for example in U.S. Patent 3,539,794 patented November 10, 1970.
  • hydroperoxide component which is not stable in polyethylene, will be quite stable when stored in a container made of the laminate material of the invention, with the polypropylene layer inside the container contacting the hydroperoxide.
  • Pouches were prepared using Maraflex 7F laminate (American Can Co.) Several of the pouches were charged with 0.15 molar bis(6-carbopentoxy-2,3,5-trichlorophenyl) oxalate and 0.009 molar l-chloro-9,10-bis(phenylethynyl) anthracene in dibutyl phthalate solvent, and the pouches were sealed. Similarly, several pouches were charged with 1.50 mol aqueous 90% hydrogen peroxide solution and 2.0 x 10 molar sodium salicylate in a solvent consisting of 80% by volume of dimethyl phthalate and 20% by volume of t-butyl alcohol and sealed. The sealed pouches with the contents described were stored at room temperature and at 40°C for 1, 3 and 6 months before testing. Control samples were prepared similarly and tested immediately.
  • the components were mixed and light intensity values were measured every two minutes in a mono- chromatorphotomultiplier light measuring instrument.
  • the measurements were transmitted to computer programmed to calculate the time-intensity and other values shown in the Tables.
  • the computer program yields time-intensity readings for each sample, in both lumens/liter and in einsteins/sec/ ml, along with light capacity, TO.75 and Quantum yield.
  • Calibration for absolute light intensities were carried out using the spectroradiometerluminometer developed by.B.G. Roberts and R.C. Hirt, Applied Spectroscopy 21,250 (1967).

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Electromagnetism (AREA)
  • General Engineering & Computer Science (AREA)
  • Packages (AREA)
  • Luminescent Compositions (AREA)

Abstract

In a chemiluminescent lighting system having separated components in storage before use, at least one of the separate components is stored in a container made from a laminate of polypropylene film and aluminium foil. Good stability of both oxalate ester components and hydroperoxide components when stored in such containers is demonstrated.

Description

    Field of the Invention
  • This invention relates to chemiluminescent compositions and to a method and packaging material for improving the storage stability of chemiluminescent components.
    • Background of the Invention
  • Chemiluminescence is obtained when certain chemiluminescent compounds, for instance oxalic-type compounds, such as oxalic acid esters, are contacted in the presence of a fluorescer with a hydrogen peroxide compound. Such a system is described in U.S. Patent 3,597,362, the disclosure of which is incorporated herein by reference. Packaged chemiluminescent light devices which utilize these chemiluminescent systems are described in U.S. Patents 3,511,612 and 3,576,987. A typical chemiluminescent device comprises a lightstick, i.e. a transparent or translucent flexible plastic outer tube of polyethylene or the like and within the outer tube a frangible glass inner tube. The inner tube is filled with one component of a two-component system (usually the hydroperoxide oomponent) and the outer plastic tube is filled with the other component (oxalate plus fluorescer). To operate the device, the outer flexible tube is bent, thereby breaking the glass tube to mix the two components within the transparent outer tube. Reaction of the mixture produces chemiluminescence and the tube transmits the lights.
  • In order for a chemiluminescent system to be practical it must be capable of storage for reasonable storage periods at temperatures above normal room temperature, for example, up to about 40°C, and in humid atmosphere, without undue deterioration, which would cause loss of light generating capacity when the system is activated for use.
  • In the systems described, the chemiluminescent component, for example, the oxalic acid ester, is subject to deterioration by light, heat, and humidity. Polyethylene has been the packaging material of choice for containing the oxalate component because of its low cost, ease of fabrication, and translucence. However, the polyethylene tube must be protected from moisture and light by enclosing it in an aluminum foil envelope during storage, since polyethylene is not impervious to moisture. Since the hydroperoxide component would be sensitive to storage in polyethylene, deteriorating rapidly on storage therein even at ordinary room temperature, it is preferred to contain the hydroperoxide component in the sealed inner glass vial which floats in the fluid contents of the polyethylene outer tube.
  • Aluminum foil is a satisfactory wrapper for containing the polyethylene tube in storage, provided the wrapper does not develop any leakage by ruptures, pin holes or the like. There is some difficulty in sealing an aluminum foil wrapper to make it totally impervious to moisture.
  • Rauhut, in U.S. Patent 3,974,368, disclosed a chlorosilane-passivization treatment for glass or plastic container materials, the object of which is to make the material more suitable for storage of the oxalic acid ester component. While this treatment was shown to be effective, it is costly and time consuming. Therefore, there is a need for a mterial in which the chemiluminescent components are protected from deterioration during storage.
    • Summary of the Invention
  • The present invention employs packaging material for containing one or several of the liquid components in a chemiluminescent device. This material is a laminate of aluminum foil and polypropylene film, bonded together preferably by means of a low molecular weight polypropylene adhesive.
    • Description of the Invention
  • Diaryl and dialkyl oxalates, substituted with strong electronegative groups, may be used as the chemiluminescent component, as described in U.S. Patent 3,597,362. In general, the greatest light output is expected with the oxalates derived from phenols or alcohols having a pKa value lower than 7.0. Examples include:
    • bis(4-nitrophenyl)oxalate
    • bis(6-carbopentoxy-2,3,5-trichlorophenyl)oxalate
    • bis(2,4-dinitrophenyl)oxalate, and the like.
  • The same fluorescers disclosed for use with oxalate- hydroperoxide systems in U.S. Patents 3,597,362 and 3,557,233 are useful in the present invention. Examples include:
    • 9,10-diphenylanthracene (blue emission)
    • 9,10-bis(phenylethynyl)anthracene (yellow-green)
    • 1-chloro-9,10-bis (phenylethynyl)anthracene(yellow-green
    • 2-chloro-9,10-bis(phenylethynyl)anthracene (yellow)
    • l,5-dichloro-9,10-bis(phenylethynyl)anthracene (yellow)
    • 1,8-dichloro-9,10-bis(phenylethynyl)anthracene (yellow)
    • 5,12-bis(phenylethynyl)naphthacene (red) rubrene (orange), and the like.
  • Suitable organic solvents (for example, dibutyl phthalate) and rate-regulating catalysts are described in U.S. Patent 3,576,987.
  • Each of the several liquid components of a chemiluminescent system of the kind described can be effectively stored in a container of the laminate material of the invention. The laminate is an aluminum foil bonded to a cast polypropylene film. Suitably the polypropylene film has a thickness of about 0.5 to 4 mils, and contains a food grade antioxidant additive. The bonding adhesive for the laminate preferably is a low molecular weight polypropylene. A suitable laminate is available from American Can Co. under the Trade name Maraflex 7F. At least one of the chemiluminescent components is stored in a container made of the laminate with the contents in contact with the polypropylene surface of the laminate material.
  • The laminate is not suitable for use as a material for the outer container of a lighting device, because it cannot transmit chemiluminescence. The laminate is nonetheless useful as a storage container for one or several of the liquid chemiluminescent components in a chemiluminescent device to protect the contents from light, air and moisture. A package made of the laminate material can be used in lighting devices of diverse shapes and designs, provided that the construction of the lighting device comprises means to rupture the laminate package and allow the contents thereof to mix and react to produce chemiluminescence within a translucent outer container.. Devices of this kind were described for example in U.S. Patent 3,539,794 patented November 10, 1970.
  • It has been discovered, quite unexpectedly, that the hydroperoxide component, which is not stable in polyethylene, will be quite stable when stored in a container made of the laminate material of the invention, with the polypropylene layer inside the container contacting the hydroperoxide.
  • The following examples illustrate the invention. Preparation of Samples
  • Pouches were prepared using Maraflex 7F laminate (American Can Co.) Several of the pouches were charged with 0.15 molar bis(6-carbopentoxy-2,3,5-trichlorophenyl) oxalate and 0.009 molar l-chloro-9,10-bis(phenylethynyl) anthracene in dibutyl phthalate solvent, and the pouches were sealed. Similarly, several pouches were charged with 1.50 mol aqueous 90% hydrogen peroxide solution and 2.0 x 10 molar sodium salicylate in a solvent consisting of 80% by volume of dimethyl phthalate and 20% by volume of t-butyl alcohol and sealed. The sealed pouches with the contents described were stored at room temperature and at 40°C for 1, 3 and 6 months before testing. Control samples were prepared similarly and tested immediately.
    • Testing Procedure
  • Measured amounts of the oxalate component and activator component prepared as described, were tested when freshly made and after storage for measured periods in the pouches described. The components were mixed and light intensity values were measured every two minutes in a mono- chromatorphotomultiplier light measuring instrument. The measurements were transmitted to computer programmed to calculate the time-intensity and other values shown in the Tables. The computer program yields time-intensity readings for each sample, in both lumens/liter and in einsteins/sec/ ml, along with light capacity, TO.75 and Quantum yield. Calibration for absolute light intensities were carried out using the spectroradiometerluminometer developed by.B.G. Roberts and R.C. Hirt, Applied Spectroscopy 21,250 (1967).
    • Results
  • Results of the testing procedure for samples 1-12 are given in Table I.
    Figure imgb0001
    Figure imgb0002
  • The results in Table I demonstrate that neither the performance of the oxalate ester components nor that of the hydrogen peroxide component, with regard to light production, has been essentially changed when those components have been separately stored in sealed containers made with the laminate of this invention for periods up to three months at temperatures at least as high as 40°C. The loss in storage for six months is remarkably small under the circumstances.

Claims (4)

1. A method for protecting the liquid components of an oxalic acid ester-hydroperoxide chemiluminescent system from deterioration and subsequent loss of light capacity on storage in the presence of elevated temperature and humidity which comprises storing the respective oxalate ester and hydroperoxide components in separate containers with at least one of the respective oxalate ester and hydroperoxide components of said system sealed in a container constructed of a laminate material having an aluminum foil layer bonded to a cast polypropylene film layer, said component being in contact with the cast polypropylene layer inside said container.
2. A method according to Claim 1, wherein said laiminate is bonded by means of a low molecular weight polypropylene adhesive.
3. An oxalic acid ester - hydroperoxide chemiluminescent light-generating system characterized in that the oxalate ester and hydroperoxide components are stored prior to mixing in separate containers, at least one of said components being sealed in a container constructed of a laminate material having an aluminum foil layer bonded to a cast polypropylene film layer, the component being in contact with the cast polypropylene layer inside said container.
4. A system according to Claim 3, wherein said laminate is bonded by means of a low molecular weight polypropylene adhesive.
EP79301723A 1978-11-24 1979-08-22 A method for protecting the liquid components of a chemiluminescent system and a chemiluminescent light-generating system thus protected Withdrawn EP0011911A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US96354378A 1978-11-24 1978-11-24
US963543 1997-11-03

Publications (1)

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EP0011911A1 true EP0011911A1 (en) 1980-06-11

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EP (1) EP0011911A1 (en)
JP (1) JPS5571784A (en)
AR (1) AR219621A1 (en)
AU (1) AU5024679A (en)
BR (1) BR7906229A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0980906A2 (en) * 1998-08-17 2000-02-23 Omniglow Corporation Chemiluminescent packaging
WO2001066994A1 (en) * 2000-03-10 2001-09-13 Continental Structures Sprl Chemiluminescent illuminating element
WO2003023275A1 (en) * 2001-09-07 2003-03-20 Omniglow Corporation Chemiluminescent lighting element
EP1676114A2 (en) * 2003-09-26 2006-07-05 Formaglow Ltd Multi-shape and multi-color chemiluminescent device
CN102582956A (en) * 2012-02-27 2012-07-18 金朝阳 Breakable storing device for chemiluminescence agent

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3584211A (en) * 1968-10-07 1971-06-08 American Cyanamid Co Chemiluminescent liquid dispensing or display container
US3808414A (en) * 1972-12-21 1974-04-30 American Cyanamid Co Device for the packaging of a three or more component chemiluminescent system
US3819925A (en) * 1973-03-12 1974-06-25 Us Navy Chemiluminescent device
US4104708A (en) * 1974-07-08 1978-08-01 The United States Of America As Represented By The Secretary Of The Navy Shrouded chemical light source
FR2386402A1 (en) * 1977-04-06 1978-11-03 Raffinage Cie Francaise PROCESS FOR COATING A SUPPORT WITH A POLYMER LAYER AND APPLICATIONS OF SUCH PROCESS

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3584211A (en) * 1968-10-07 1971-06-08 American Cyanamid Co Chemiluminescent liquid dispensing or display container
US3808414A (en) * 1972-12-21 1974-04-30 American Cyanamid Co Device for the packaging of a three or more component chemiluminescent system
US3819925A (en) * 1973-03-12 1974-06-25 Us Navy Chemiluminescent device
US4104708A (en) * 1974-07-08 1978-08-01 The United States Of America As Represented By The Secretary Of The Navy Shrouded chemical light source
FR2386402A1 (en) * 1977-04-06 1978-11-03 Raffinage Cie Francaise PROCESS FOR COATING A SUPPORT WITH A POLYMER LAYER AND APPLICATIONS OF SUCH PROCESS

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0980906A2 (en) * 1998-08-17 2000-02-23 Omniglow Corporation Chemiluminescent packaging
EP0980906A3 (en) * 1998-08-17 2000-12-13 Omniglow Corporation Chemiluminescent packaging
WO2001066994A1 (en) * 2000-03-10 2001-09-13 Continental Structures Sprl Chemiluminescent illuminating element
AU783847B2 (en) * 2000-03-10 2005-12-15 Omniglow Corporation Chemiluminescent illuminating element
KR100847195B1 (en) * 2000-03-10 2008-07-17 사이륨 테크놀로지즈 인코포레이티드 Chemiluminescent illuminating element
WO2003023275A1 (en) * 2001-09-07 2003-03-20 Omniglow Corporation Chemiluminescent lighting element
EP1676114A2 (en) * 2003-09-26 2006-07-05 Formaglow Ltd Multi-shape and multi-color chemiluminescent device
EP1676114A4 (en) * 2003-09-26 2009-05-13 Formaglow Ltd Multi-shape and multi-color chemiluminescent device
CN102582956A (en) * 2012-02-27 2012-07-18 金朝阳 Breakable storing device for chemiluminescence agent

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AU5024679A (en) 1980-05-29
AR219621A1 (en) 1980-08-29
JPS5571784A (en) 1980-05-30
BR7906229A (en) 1980-05-27

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